Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis
Jens Christoffers (Editor), Angelika Baro (Editor), Steven V. Ley (Foreword by)
IN: 978-3-527-31107-1
Hardcover
359 pages
January 2006
Filling the gap in the literature, this book presents everything there is to know about this topic. By comprehensively covering the quaternary stereocenters found in a range of important and useful molecules in pharmaceutical and medicinal applications, as well as in thousands of natural products, the book provides the know-how chemists need to synthesize challenging molecules with numerous applications.
A must for organic chemists in academia, the pharmaceutical industry and medicine.
Table of Contents
1 Important Natural Products (Hirokazu Arimoto and Daisuke Uemura).
1.1 Introduction.
1.2 Alkylation of Tertiary Carbon Centers.
1.3 Cycloaddition to Alkenes.
1.4 Rearrangement Reactions.
1.5 Carbometallation Reactions.
1.6 C–H Functionalization Reactions.
1.7 Asymmetric Modification of Enantiotopic/Diastereotopic Substituents of Quaternary Carbon Centers.
1.8 Summary.
2 Important Pharmaceuticals and Intermediates (Johannes G. de Vries).
2.1 The Chirality of Drugs and Agrochemicals.
2.2 Steroids.
2.3 Pharmaceuticals and Agrochemicals Based on á-Dialkylated Amino Acids.
2.4 Azole Antimycotics.
2.5 Alkaloids.
2.6 HIV Inhibitors.
2.7 β-Lactam Antibiotics.
2.8 The Tetracyclines.
2.9 Summary and Outlook.
3 Aldol Reactions (Bernd Schetter and Rainer Mahrwald).
3.1 Introduction.
3.2 Metal Enolates.
3.3 Catalytic Aldol Additions.
3.4 Conclusions.
3.5 Note Added in Proof 79
4 Michael Reactions and Conjugate Additions (Angelika Baro and Jens Christoffers).
4.1 Introduction.
4.2 Chiral Brönstedt Bases.
4.3 Chiral Metal Complexes.
4.4 Chiral Auxiliaries.
5 Rearrangement Reactions (Annett Pollex and Martin Hiersemann).
5.1 Introduction.
5.2 Applications.
5.3 Summary.
6 Cycloaddition Reactions (Giovanni Desimoni and Givseppe Faita).
6.1 Introduction.
6.2 [2+1] Cycloaddition Reactions.
6.3 [2+2] Cycloaddition Reactions.
6.4 1,3-Dipolar Cycloaddition Reactions.
6.5 Diels–Alder Reactions.
6.6 Hetero-Diels–Alder Reactions.
6.7 Consecutive Cycloaddition Reactions.
7 Asymmetric Cross-coupling and Mizoroki–Heck Reactions (Louis Barriault and Effiette L. O. Sauer).
7.1 The Asymmetric Heck Reaction.
7.2 Metal-catalyzed Cross-coupling Reactions.
7.3 Summary.
8 Alkylation of Ketones and Imines (Diego J. Ramón and Miguel Yus).
8.1 Introduction.
8.2 Diastereoselective Additions.
8.3 Enantioselective Additions by Modulated Processes.
8.4 Enantioselective Additions by Promoted Processes.
9 Asymmetric Allylic Alkylation (Manfred Braun).
9.1 Introduction.
9.2 Electrophilic Allylic Alkylation.
9.3 Nucleophilic Allylic Alkylation.
9.4 Miscellaneous Methods.
9.5 Outlook.
10 Phase-Transfer Catalysis (Takashi Ooi and Keiji Maruoka).
10.1 Introduction.
10.2 Carbon–Carbon Bond Formation Through PTC.
10.3 Carbon–Heteroatom Bond Formation Through PTC.
10.4 Conclusion.
11 Radical Reactions (Kalyani Patil and Mukund P. Sibi).
11.1 Introduction.
11.2 Radical Cyclization.
11.3 Atom- and Group-transfer Cyclizations.
11.4 Intermolecular Radical Allylations.
11.5 Other Metallic Reagents.
11.6 Radical Reactions in the Solid State.
11.7 Conclusion.
11.8 Experimental.
12 Enzymatic Methods (Uwe T. Bornscheuer, Erik Henke, and Jürgen Pleiss).
12.1 Introduction.
12.2 Strategies for the Kinetic Resolution of Sterically Demanding Substrates.
12.3 Conclusion.
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